The Hard Part with Evan McCann

Ian MacKinnon is the Co-Founder of Stingray Security. Real-time protection from online scams, phishing, and fake websites. Ian previously Co-Founded Later.com Chapters 00:00 The Evolution of AI-Driven Phishing 03:57 Consumer and Corporate Perspectives on Phishing 08:17 The Role of Technology in Phishing Attacks 11:58 Identifying and Preventing Scams 16:28 The Future of Phishing and AI Tools 21:27 Building Trust in a Digital World 27:03 Mobile Vulnerabilities and Phishing Risks 29:37 Deepfakes and Voice Cloning in Phishing 34:34 The Ongoing Battle Against Phishing

Robert Farlow is the Co-Founder and CEO of Plato. Training Environments for Browser Agents Chapters 00:00 The Genesis of Browser Agents 02:38 Building Universal Agents 05:25 Training Models and Learning Mechanisms 08:02 The Future of Browsers and Agents 10:39 Trust and Error Management in Automation 13:39 Synthetic Data and Edge Cases 16:15 Complexity in Multi-Step Tasks 18:53 Navigating the AI Landscape 21:39 The Data Wars and Business Incentives 24:07 The Evolution of User Interfaces 26:36 Building in San Francisco 28:57 The Role of AI in Team Dynamics 31:45 Resilience in Entrepreneurship

Brent Lane is the CEO of BigGeo. BigGeo is transforming how the world works with geospatial data. With innovative technology and industry-leading speed, they empower organizations to visualize, interact with, and unlock the full potential of location-based insights—at any scale. Chapters 00:00 Understanding Geospatial Data 02:45 The Importance of Location-Based Context 05:37 Infrastructure Challenges in Geospatial Data 08:09 The Future of Spatial Analytics 11:03 Monetization of Geospatial Data 13:53 Building a Unified Data Platform 16:42 The Role of AI in Geospatial Data 19:29 Navigating Sovereign Data and Cloud Solutions 22:14 Team Dynamics in a Tech-Driven World 25:02 Finding Balance in Business and Life

Ignacio Tartavull is the CEO of Pinkbot. Pinkbot builds robots that make last-mile delivery faster, cheaper and greener. Chapters 00:00 Intro 1:45 From Education to Neuroscience: The Journey Begins 02:33 The Shift to Autonomous Driving: A New Challenge 05:34 Navigating City Regulations: The Toronto Experience 08:13 Logistics of Robot Deliveries: How It Works 10:46 Real-World Challenges: Interacting with the Environment 13:51 Financial Aspects: Cost-Effectiveness of Delivery Robots 16:31 Business Model: Partnering with Restaurants 19:23 The Future of Autonomous Vehicles: A Long Road Ahead 22:13 The Future of Delivery Platforms 23:34 Weather Challenges in Delivery 24:39 Enterprise Partnerships and Their Impact 27:26 Insights from Being a Courier 32:19 The Future of Delivery Beyond Food 34:01 Regulatory Considerations for Delivery Robots 35:38 Urban vs. Suburban Delivery Dynamics 38:06 Building a Robotics Company 40:26 Designing for the Future of Transportation 41:20 Overcoming Challenges in Business

Ben Vinegar is the Co-Founder of Modem. Modem is your auto-triage Product Manager. Modem turns scattered feedback – from users, teammates, and software – into actionable, living issues. Save time, reduce bottlenecks, and ship faster. Chapters 00:00 Intro 1:45 The Future of Developer Tools 05:35 The Changing Role of Software Engineers 15:04 Open Source in the Age of AI 19:02 Stickiness of Developer Tools 20:34 The Evolution of Developer Tools 27:58 Hiring in the Modern Tech Landscape 31:24 The Toronto Tech Scene vs. San Francisco 38:20 Resilience in Entrepreneurship

Justin Sky is the CEO and Co-Founder of Rose Rocket. Rose Rocket is a SaaS-based Transportation Management System (TMS) specializing in workflow automation for Enterprise and SMB transport companies. Chapters 00:00 Intro 1:40 Acquisitions and Strategic Fit 02:18 Leveraging AI and LLMs in Business 04:41 Replatforming for Future Growth 07:44 The Surge of New Players in Transportation Tech 10:58 Understanding the Transportation Industry 13:42 The Future of Autonomous Trucks 15:32 Industry Dynamics and Consolidation Trends 17:59 Advice for Founders in Traditional Industries 21:23 Hiring for Culture and Values 24:39 The Evolution of Y Combinator 27:14 Refilling the Founder’s Tank 30:42 Navigating the Toronto Ecosystem 33:02 Strategic Fundraising Insights 35:03 Building a Diverse and Effective Board 37:16 The Toronto Tech Scene: Growth and Challenges 40:15 Lessons from the Journey of Entrepreneurship

Elan Lee is the CEO of Exploding Kittens. Chapters 00:00 Intro 1:40 Designing Engaging Games 02:49 The Importance of Player Feedback 05:28 Accessibility and Player Experience 08:22 The Golden Age of Tabletop Games 11:25 Kickstarter Success Strategies 13:54 Building and Sustaining Community 16:53 Quality Control in Physical Games 19:25 Expansions and Game Evolution 21:38 Retail Dynamics in Tabletop Games 23:26 Balancing Creativity and Business 26:13 Persistence in Game Development 28:20 Team Structure and Internal Operations 28:47 Understanding Customer Needs 31:12 Designing for Social Interaction 32:21 Innovation vs. Remakes in Gaming 34:21 The Testing and Refinement Process 37:19 Balancing Rigour with Timelines 38:59 Recognizing Joy in Gameplay 39:55 Coping with Hard Times

Ahmed Nimale is the Co-Founder and CEO of KYD Labs. Chapters 00:00 Intro 1:40 The Journey into Live Entertainment 02:56 Understanding the Ticketing Landscape 05:35 The Role of Venues and Ticketing Platforms 08:20 Marketing Challenges in Live Events 11:28 Financial Dynamics of Live Entertainment 14:17 The Future of Ticket Pricing 17:01 The Impact of Resale Markets 20:13 The Role of AI and Technology in Live Events 22:57 Direct Artist-Fan Relationships 25:18 The Evolution of Music Financing 28:24 The Future of Live Event Production 31:17 The Intersection of Crypto and Live Events 34:03 Artist Engagement and Fan Loyalty 37:01 Navigating the Music Industry's Financial Landscape 39:48 Finding Balance as a Founder

Doug Roseborough spent his career at multiple leading technology companies including 30 plus years at Oracle. Chapters 00:00 Intro 1:40 Early Days at Oracle 02:56 Oracle's Secret Sauce 05:16 Transition to the Bay Area 08:15 Rolling Out Pricing Models 10:31 Cultural Insights at Oracle 13:05 Leadership and Team Dynamics 15:35 Operations at Oracle 17:59 Effective Meetings 20:38 Customer Engagement Strategies 23:00 Startup Advice 25:37 Navigating a Noisy Market 28:11 Bay Area Mentality 30:31 Career Reflections and AI Impact 33:06 Dealing with Hard Times

Tamer Shahin and Jerry Chen are the Co-Founders of Hiro. Hiro improves child health by turning physiotherapy into fun, interactive, movement-based games designed for kids of all abilities. Chapters 00:00 Intro 1:40 Inspiration Behind Hero 02:55 Understanding Therapy for Children with Disabilities 06:19 Gamifying Physiotherapy: The Solution 08:25 Accessibility and Convenience in Physiotherapy 11:39 Leveraging Technology for Progress Tracking 14:02 Feedback from Parents and Therapists 14:47 Pricing and Accessibility Considerations 15:58 Market Size and Potential 17:39 Product Development and Iteration 22:25 Engaging with Families for Feedback 26:14 Addressing Therapist Shortages 27:31 Government Partnerships and Support 28:06 Overcoming Challenges as Founders

Cameron Conn is the CEO of Champlain. Cameron previously Co-Founded OneComply (acquired by GeoComply). Chapters 00:00 Intro 1:40 Cameron's Journey Through Industries 07:51 Transitioning to Retail and Learning the Ropes 12:14 Positioning and Pricing Strategies in Apparel 19:11 Navigating Wholesale and Direct-to-Consumer Channels 26:25 Navigating Industry Challenges 27:36 The Vancouver Apparel Scene 29:53 Understanding Manufacturing Relationships 33:00 Designing Collections with Purpose 35:22 The Value of Collaborations 39:42 Complexity in Apparel Collections 43:55 The Investment Landscape in Apparel 48:30 Overcoming Hard Times

Robert Saunders is the Co-Founder and CEO of Ownright. Ownright simplifies real estate transactions with the perfect combination of expert legal guidance, a client-first approach, and efficient technology. Chapters 00:00 Intro 1:40 The Genesis of Ownright 07:14 Navigating Regulatory Challenges 13:14 Financial Hurdles in Real Estate Transactions 17:28 Growth Strategies and Market Expansion 20:50 Understanding Pricing and Unit Economics 24:38 Leveraging AI for Efficiency 32:11 The Future of PropTech 37:23 The Rebranding Journey 41:36 Finding Balance in Entrepreneurship

Brennan Spellacy is the Co-Founder and CEO of Patch. Patch combines technology and carbon markets expertise to help companies build and execute their carbon credit strategies from end to end, channelling capital into critical climate solutions. Chapters 0:00 Intro 1:40 The Evolution of Sonder: From Flatbook to Hospitality Innovator 06:41 Transitioning to Patch: The Journey to Founding a Climate Solution 11:07 Understanding Carbon Markets: The Role of Patch in Sustainability 16:09 Navigating Complexity: Strategies for Chief Sustainability Officers 20:43 Crafting Effective Sustainability Strategies: Insights from Patch 24:21 Strategic Procurement in Carbon Credits 27:49 Navigating Global Projects and Technology Risks 31:28 Understanding the Global Carbon Market Landscape 35:14 Pricing Dynamics and Industry-Specific Strategies 38:58 Future Trends in Carbon Markets and Technology 43:40 Resilience in Entrepreneurship 45:44 Engagement and Community Building

Francois Lafortune is the Co-Founder and CEO of Diagram Ventures. Francois is also a Managing Partner at Sagard and Chairman of the Board at Nesto. Diagram is a venture launchpad building the next generation of global companies based in Canada. They develop and incubate our own ideas, and find exceptional entrepreneurs and technologists to build companies with us. Chapters 00:00 Introduction 2:00 The Genesis of Diagram: A Venture Studio's Origin 05:23 Navigating the Idea Flow: From Concept to Execution 09:49 Criteria for Success: Understanding the Venture Creation Funnel 13:54 Leveraging Competitive Advantage: The Diagram Ecosystem 16:36 Finding the Right Founders: The CEO Search Process 21:14 Funding Dynamics: Balancing Ownership and Attracting Investors 24:37 Team Structure: Blending Operators and Investors 27:18 Navigating the Entrepreneurial Landscape 28:51 Identifying Market Opportunities 31:05 Learning from Experience 36:51 Signals of Success 39:35 Emerging Trends Beyond AI 41:04 Balancing Ideas and Execution 44:15 Transitioning from Hands-On to Hands-Off 46:41 Coping with Challenges in Entrepreneurship

Rishard Rameez is the Co-Founder and CEO of Zown. Zown is a buyer-first real estate platform operating in both Canada and the U.S., built to reward and empower people to reach their homeownership dreams faster. Through their model, buyers receive up to $25,000 toward their home purchase — funded through the commission Zown earns. There’s no repayment, and buyers keep full ownership from day one. Chapters 00:00 Podcast Introduction 2:00 The Spark of Innovation: A Reddit Post 04:43 Identifying the Gaps in Real Estate Services 11:16 Transforming Home Buying: The Financial Impact 13:23 Overcoming Traditional Barriers in Real Estate 14:46 Expanding Horizons: Geographic Growth and Market Dynamics 16:25 Understanding the Real Estate Commission Structure 20:30 Leveraging Technology for Scalability 23:12 Marketing Strategies in a Noisy Market 25:51 Navigating Market Dynamics and Economic Factors 30:23 Finding Purpose in Hard Times

Michael Serbinis is the Founder and CEO of League. Founded in 2014, League is the leading healthcare consumer experience platform, reaching more than 40 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high-engagement healthcare solutions proven to improve health outcomes. League has raised $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart. Chapters 00:00 Podcast Introduction 2:00 Getting Shit Done: The Core Philosophy 07:02 Healthcare Challenges: Access and Understanding 13:20 The Agentic Era: AI in Healthcare 19:30 Learning and Adapting: The Key to Success 22:23 Partnerships: Transforming Healthcare Together 26:18 League's Platform Approach: A New Era in Healthcare 31:49 Balancing Family and Business: A Personal Journey 36:18 Perseverance in Hard Times: Lessons Learned

Nicholas Chepesiuk is the VP of Innovation at Qualifacts. Nicholas was the Founder & CEO of OnCall Health, which was acquired by Qualifacts in 2022. Chapters 00:00 Podcast Introduction 2:00 Foundational Experiences in Early Roles 07:21 Telehealth Surge: Impact of the Pandemic 12:53 Post-Acquisition Insights and Growth Strategies 18:06 Trends and Opportunities in Healthcare 23:19 Building a Strong Company Culture 28:21 Personal Resilience and Coping Mechanisms

Derrick Emsley is the Co-Founder of tentree and veritree. Chapters 00:00 Podcast Introduction 2:00 The Genesis of Tentree 05:04 Lessons Learned in Entrepreneurship 07:36 Transitioning to Veritree 09:07 Navigating the Climate Tech Landscape 12:07 Project Selection and Impact 14:52 Building Partnerships and Verification 17:37 The Importance of Trees 20:24 Consumer Behavior and Local Impact 23:12 Trends in Sustainability 25:52 Metrics and ROI in Sustainability 28:38 Learning and Growth as a Founder 31:26 Team Dynamics and Culture 34:09 The Role of Impact in Business 37:01 Technology in Tracking Projects 39:52 Overcoming Challenges in Entrepreneurship

Chloe Liang is the Co-Founder of Cocasa. Cocasa is revolutionizing travel and property ownership by allowing members to buy equity in luxurious holiday homes from €39,000/10% share. Chapters 00:00 Podcast Introduction 2:00 From Banking to Founding: Chloe's Journey 10:31 Identifying the Problem: Cocasa's Mission 21:08 Understanding the Cocasa Model 35:25 Navigating Challenges as a Founder 40:06 Engagement and Community Building

Kyle Norton is the Chief Revenue Officer at Owner. Chapters 0:00 Podcast Intro 2:00 Evaluating Companies: The Key Factors 07:38 Building a Revenue Team: Initial Steps and Strategies 11:39 Quality Over Quantity: The Importance of Revenue Quality 15:49 AI in Sales: Internal and External Impacts 20:42 Navigating the Changing Landscape of Outbound Sales 26:58 Hiring for Success: Qualities in Sales Roles 33:15 The Hybrid Work Debate: In-Person vs Remote 38:47 Geographic Strategy: Where to Position Sales Reps 44:09 Continuous Learning: The Benefits of Advisory Roles 47:20 Resilience in Sales: Maintaining Drive Through Challenges 52:31 Introduction to the Hard Part Podcast 52:31 Engagement and Community Building